I am running Asterisk in a guest OS on Microsoft Hyper-V and I chose to use the license on USB key activation option. How do I connect the USB key to the guest?

I've used VMware before and I know it's easy to pass through a USB device with VMware, but Microsoft has chosen to make this painful. Is there a workaround or do I need to change activation types? (you mentioned I could return the USB keys if I wanted to change)

In order to connect a USB device to a Hyper-V guest you need to use a USB over IP solution. This means you plug the USB device into a real (physical) device(possibly even the Hyper-V host) and then attach it to the guest over a network (IP) connection.

For example, there are software packages which will share a USB device over an IP connection:

Some clients have used a Raspberry Pi to create a USB device server on their network for USB keys and other devices shared across their data center.

We try to avoid endorsing third party products unless we continually test their product with our dongles (which we do not at this time), but we have been told by customers that they have had success with a couple of the software packages above.